1. Technical Field of the Invention
The present invention relates to novel fluoro dimethicone copolyol ester compounds in which the fluoro group is attached to the silicon atom through a fatty group by means of an ester linkage, and a water-soluble group is connected to a different silicon atom. This invention also relates a series of such products having differing amounts of water-soluble groups, silicone soluble groups fatty soluble groups and fluoro-soluble groups. By careful selection of the compounds so constructed, very efficient mild conditioning agents may be achieved.
2. Description of the Arts
There have been several fluoro silicone compounds disclosed in the art. They include U.S. Pat. No.5,446,114 to O""Lenick issued August 1995. This patent teaches that xe2x80x9cthe compounds of the invention are prepared by reacting a silanic hydrogen containing silicone polymer with a vinyl containing fluoro compound and an allyl alcohol alkoxylate.xe2x80x9d This results in a molecule with two functional groups water soluble groups and fluoro groups, both independently linked to a different silicon atom.
U.S. Pat. No. 5,473,038 to O""Lenick issued December 1995 teaches that xe2x80x9ccompounds of the invention are prepared by reacting a silanic hydrogen containing silicone polymer with a vinyl containing fluoro compound alpha olefinxe2x80x9d. This results in a molecule with two functional groups alkyl groups and fluoro groups, both independently linked to a different silicon atom.
U.S. Pat. No. 6,087,517 to O""Lenick issued July 2000, teaches xe2x80x9cthe invention relates to a series of novel silicone fluorinated dimethicone copolyol phosphates. The compounds of the invention are prepared by reacting a fluoro dimethicone copolyol disclosed in U.S. Pat. No. 5,446,144 with a suitable phosphating agent.xe2x80x9d This invention introduces a phosphate group onto the hydroxyl functional group of the compounds of U.S. 5,446,144. This results in a molecule with two functional groups alkyl groups and fluoro groups, both independently linked to a different silicon atom.
U.S. Pat. No. 6,008,397 to O""Lenick, issued Dec. 28, 1999, xe2x80x9cdiscloses novel fluoro esters made by reacting (a) a carboxy silicone, and (b) the hydroxyl group of fluoro alcohol.xe2x80x9d The compounds of the ""397 invention contain short linking groups derived from anhydrides and link the fluoro group through the water soluble group to one silicon atom.
We have surprisingly found that products made by the reaction of silicone methyl ester having 11 carbon atoms directly with the fluoro group, having the water soluble group on another silicon atom results in a fluoro-fatty silicone dimethicone copolyol. The compounds give unique emulsification properties with fluoro and fatty compounds or both, and have an outstanding gloss when applied to the skin.
We have also surprisingly found that by having a bulky alkyl group linked to silicone, unique skin feel and conditioning properties result. The compounds of the prior art have the ester moiety linked through a water-soluble polyoxyalkylene group, resulting in a surface-active agent with different properties than the compounds of the present invention. The compounds linked through the polyoxyalkylene group are less efficient emulsifiers and do not provide the same degree of conditioning to the skin.
The present invention is directed toward the providing a series of novel silicone compounds that have a C-11 alkyl group linked through an ester linkage to a fluoro group and a silicon atom on opposite ends of the molecule. One side of the C11 is linked through a carbon silicon bond and on the other end of the C11 group is linked a fluoro group. A water-soluble hydroxyl groups are likewise linked directly to another silicon group.
The compounds of the present invention have the formula: 
wherein;
a is an integer ranging from 0 to 2000;
b is an integer ranging from 1 to 20;
c is an integer ranging from 1 to 20;
d is an integer ranging from 0 to 20;
n is an integer ranging from 10 to 20;
x is an integer ranging 0 to 20;
y is an integer ranging 0 to 20;
z is an integer ranging 0 to 20;
R1 is
CF3xe2x80x94(CF2)mxe2x80x94CH2CH2xe2x80x94Oxe2x80x94;
m is an integer ranging from 3 to 18.
It is the object of the present invention is the provision of a series of novel silicone compounds that have specific hydrophilic ester groups linked through an 11-carbon linkage directly to silicon in a dimethicone backbone
The compounds of the present invention conform to the formula; 
wherein;
a is an integer ranging from 0 to 2000;
b is an integer ranging from 1 to 20;
c is an integer ranging from 1 to 20;
d is an integer ranging from 0 to 20;
n is an integer ranging from 10 to 20;
x is an integer ranging 0 to 20;
y is an integer ranging 0 to 20;
z is an integer ranging 0 to 20;
R1 is
CF3xe2x80x94(CF2)mxe2x80x94CH2CH2xe2x80x94Oxe2x80x94;
m is an integer ranging from 3 to 18.
The products are made by reacting the following compounds with fluoro alcohols to give the compounds of the present invention. 
wherein;
a is an integer ranging from 0 to 2000;
b is an integer ranging from 1 to 20;
c is an integer ranging from 1 to 20;
d is an integer ranging from 0 to 20;
n is an integer ranging from 10 to 20;
x is an integer ranging 0 to 20;
y is an integer ranging 0 to 20;
z is an integer ranging 0 to 20.
The methyl ester is prepared by the hydrosilylation reaction of a silicone polymer and specific alpha vinyl compounds. 
wherein;
a is an integer ranging from 0 to 2000;
b is an integer ranging from 1 to 20;
c is an integer ranging from 1 to 20;
d is an integer ranging from 0 to 20;
n is an integer ranging from 10 to 20;
x is an integer ranging 0 to 20;
y is an integer ranging 0 to 20;
z is an integer ranging 0 to 20.
The preparation of the intermediate is critical to the synthesis of the compounds of the present invention. If one tries to hydrosilylate a carboxylic acid directly, the reaction fails. The carboxylic acid group reacts with the Sixe2x80x94H and the desired product is not achieved. The hydrosilylation using the methyl ester however is essentially quantitative and proceeds to give the desired product.
In a preferred embodiment of the silicone polymer set d is 0.
In a preferred embodiment of the silicone polymer set d is an integer ranging from 1 to 20.
In a preferred embodiment of the silicone polymer set b in an integer ranging from 1 to 5.
In a preferred embodiment of the silicone polymer set b is an integer ranging from 6 to 20.
In a preferred embodiment of the silicone polymer set c is an integer ranging from 1 to 5.
In a preferred embodiment of the silicone polymer set c in an integer ranging from 6 to 20.
In a preferred embodiment of the silicone polymer set a is an integer ranging from 1 to 5.
In a preferred embodiment of the silicone polymer set a in an integer ranging from 6 to 20.